Nitriles-buliding-blocks

939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 939-80-0

Example 224 Preparation of 6-L-CYCLOHEXYL-5- (1H-TETRAZOL-5-YL)-1H-BENZIMIDAZOL-2-VLL-2- PHENYLQUINOXALINE (Compound 258) Step 1: 4-CYCLOHEXYLAMINO-3-NITROBENZONITRILE (Compound 127); [0776] A solution of 1 g (5.48 mmol) 4-CHLORO-3-NITROBENZONITRILE, Compound 126, and 1.14 g (11. 51 mmol) of cyclohexylamine were heated overnight in 5 mL anhydrous DMF. After cooling to room temperature, the solution was added dropwise into 100 mL H20 stirring vigorously. The solids were collected by filtration and dried under vacuum yielding 1.34 g (100%) bright yellow solids which were used as such without analysis in the next step.

Statistics shows that 939-80-0 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-nitrobenzonitrile.

Reference:
Patent; GENELABS TECHNOLOGIES, INC; WO2005/12288; (2005); A1;,
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103146-25-4, Name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 103146-25-4, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

50 gm of 5-Cyano phthalide was stirred in 150 ml of THF at -5C. 227 gm of l-(4-fluorophenyl) magnesium bromide was added to the above solution and stirred for about 15 minutes at -5 0C. 324 gm of l-[3- (dimethylamino) propyl] magnesium chloride was added slowly to the reaction mass at -5 0C and then stirred for about 30 minutes at room temperature. The reaction mixture was quenched into cold water (650 ml). Reaction mixture pH was adjusted to about 2 with 36% aqueous HCl (94 ml) and washed the reaction mixture with toluene (2 X 150 ml). The aqueous layer was separated, toluene (300 ml) was added and pH was adjusted to about 7.5 with aqueous ammonia (45 ml). The organic layer was separated and aqueous layer was extracted with toluene (1 X 200 ml; IX 100 ml). Total organic layer was washed with water (1 X 250 ml) followed by salt solution (1 X 250 ml). The final organic layer was distilled completely under vacuum to get 76 gm of residue.The residue obtained above was charged in 150 ml of toluene, stirred at room temperature for about 1 hour. The solution was cooled to 10-150C and stirred for about 1 hour. The solid was filtered and washed with toluene. The wet solid was dried to get 55 gm of the title compound as crystalline Form S.The obtained product was analyzed by DSC and XRD, the results are as provided in Fig. 1 & 2 respectively.

Statistics shows that 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 103146-25-4.

Reference:
Patent; SHODHANA LABORATORIES LIMITED; GIRIDHAR, Thota; SRINIVASULU, Gudipati; SRINIVASA RAO, Kotaru; WO2010/4575; (2010); A2;,
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40497-11-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, This compound has unique chemical properties. The synthetic route is as follows.

0.01 mol of 2-fluoroaniline and a small amount of ethanol were placed in a 250 mL round bottom three-necked flask, and 3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise with stirring under ice bath. 0.018 mol of sodium nitrite was dissolved in 10 mL of water, and slowly dropped into the flask. After the completion of the dropwise addition, the reaction was carried out for 0.5 h to obtain a yellow diazonium salt solution.Add 0.01 mol of ethyl 2,3-dicyanopropionate to a three-necked flask.The prepared diazonium salt solution was dropped into the flask, and the reaction was added dropwise for 2 hours. Ammonia water was added, the pH was adjusted to 9-10, and the reaction was carried out for 2 h at room temperature. After completion of the reaction, the mixture was extracted with 40 mL of dichloromethane. The organic layer was washed with water (2¡Á30 mL), and washed with saturated sodium chloride solution (1¡Á40 mL), dried over anhydrous magnesium sulfate, and then evaporated. Yield 62.3%, product melting point: 196-198 C.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Nanjing Tech University; Wan Rong; Chen Fuli; Han Zhenyu; Fu Xiaohuan; Jiang Peng; (17 pag.)CN108203450; (2018); A;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 327056-73-5, name is 3-Chloro-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., 327056-73-5

To a solution of 3-chloro-5-fluorobenzonitrile (E-1, 10 g, 64.28 mmol) and 6-chloro-2-fluoro-3-methyl-phenol (E-2, 9.38 g, 58.44 mmol) in DMA (100 mL) was added Cs2CO3 (1.9 g, 5.84 mmol) followed by K2CO3 (8.9 g, 64.28 mmol). The mixture was heated to 120 C. (oil bath) under argon for 5.5 h. The reaction was cooled to RT and water (150 mL) was added. The mixture was extracted with EtOAc (150 mL) and the aqueous phase back extracted with EtOAc (2¡Á100 mL). The combined EtOAc extracts were dried (MgSO4), filtered and concentrated in vacuo afford 11.1 g (75% purity) of E-3a as a white crystalline solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Roche Palo Alto LLC; US2009/12034; (2009); A1;,
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A common compound: 31643-49-9, name is 4-Nitrophthalonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 31643-49-9

General procedure: 4-nitrophthalonitrile (0.38 g, 1.92 mmol), 2,4,6-trimethylphenylamine (0.55 g, 1.92 mmol) and anhydrous DMF(15 mL) were added to a round bottom flask under a nitrogen atmosphere.A fine powder of anhydrous potassium carbonate (0.8 g,5.76 mmol) was added to this mixture. The resulting mixture was stirredat room temperature for 24 h. The crude product was collected by filtration,washedwith distilled water, and then recrystallized. The crude productwas recrystallized from THF-petroleum ether to afford a whitepowder.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 31643-49-9, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Medyouni, Rawdha; Elgabsi, Wissal; Naouali, Olfa; Romerosa, Antonio; Sulaiman Alayed, Abdullah; Baklouti, Lasaad; Hamdi, Naceur; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 167; (2016); p. 165 – 174;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2042-37-7 name is 2-Bromobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 2042-37-7

General procedure: The tetrazole compounds were prepared by a modified literature reported protocol.3 Thus, the aromatic nitrile (1.0 equiv), TBAF.3H2O (0.5 equiv) and TMS-N3 (1.5 equiv) were taken in a screw capped vial equipped with a magnetic stirrer and the resulting mixture was stirred vigorously at 85 oC. The reaction mixture was then transferred to a seperatory funnel and TBAF was removed by washing the organic phase with 1M aqueous HCl solution (20 ml). The organic phase was separated, washed with brine (20 ml) and dried over Na2SO4 and then concentrated in a rotary evaporator. The products were then purified by silica-gel (60-120 mesh) column chromatography or for some cases by recystallisation. Compound 2L was used as a crude mixture for further reaction. The compounds were then characterized by IR, NMR spectroscopy and mass spectrometry. Compounds 2A-B and 2H are reported compounds3 whereas 2C- 2G and 2I- 2L are new.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Bag, Subhendu Sekhar; Talukdar, Sangita; Anjali; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2044 – 2050;,
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A common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 103146-25-4.

Example 2 (Preparation of the mixture used in example 1) (S)-4-[4-Dimethylamino-1-(4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethyl- benzonitrile To a stirred solution of racemic 4- [4-Dimethylamino-l- (4-fluorophenyl)-l-hydroxy- butyl] -3-hydroxymethylbenzonitrile (29 mmol, 10 g) and vinylbutyrate (58 mmol, 7,5 ml) in anhydrous 1,4-dioxane (142,5 ml) is added lipoprotein lipase pseudomonas sp. (160 U, 250 mg). The reaction is heated to 50 C and followed by HPLC. After 192 hours at a conversion of 41%, additional 250 mg lipase was added. After 504 hours, at a conversion of 63 % the reaction was stopped. The enzyme is filtered off and washed with a small amount of 1,4-dioxane. The combined organic phases are evaporated in vacuo and subsequently analyzed on super critical fluid chromatography. Obtained ee-value ( (S-diol) = 95% (S-diol/R-diol = 40: 1).

The synthetic route of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2005/77891; (2005); A1;,
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These common heterocyclic compound, 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 13388-75-5

General procedure: A 50 mL round-bottomed flask was charged with 3 (0.177 g, 1 mmol), aromatic aldehyde or substituted aromatic aldehyde (1 mmol) and 10 mL methanol with stirring, and the mixture was heated to 60 C. After 30 min, sodium methoxide (0.027 g, 0.5 mmol) was added to the mixture and keep the temperature for 4-6 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to RT, and the precipitate was separated by filter and recrystallized from methanol to give 4a-4z and 5a-5d.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 13388-75-5.

Reference:
Article; Ma, Jun; Li, Jiajun; Tian, Yu-Shun; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 81 – 85;,
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114897-91-5, A common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(11-2) According to a method similar to Example (8-1), from (4-bromo-2-fluorophenyl)acetonitrile (3.0 g, 14 mmol) obtained in Example (11-1) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.45 g, 14 mmol), (3-fluoro-4′-hydroxy-1,1′-biphenyl-4-yl)acetonitrile was obtained as a colorless solid (2.9 g, yield: 91%). 1H-NMR (400MHz, MeOH-d4): delta 7.50-7.34 (5H, m), 6.87 (2H, d, J=8.8Hz), 3.92 (2H, s).

The synthetic route of 114897-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP1806332; (2007); A1;,
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These common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 79463-77-7

To a stirred suspension of rac-allyl [3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazol-4-yl]carbamate (intermediate 7), 50.0 g (0.159 mol) in 2-propanol (860 mL) was added diphenyl N- cyanocarbonimidate, 38.0 g (0.159 mol). The reaction mixture was heated to reflux at which point the suspension dissolved into solution after a further 10 minutes at reflux a white precipitate formed. The reaction mixture was stirred at reflux for a further 1 hour before allowing to slowly cool to room temperature overnight. The precipitate was filtered, washing with diethyl ether (2 x 250 mL) and the resulting white solid was allowed to dry to yield rac-phenyl 4-{ [(allyloxy)carbonyl]amino}-N-cyano- 3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazole-l-carboximidate as a white solid, 48.6 g (67 %). NMR (400 MHz, DMSO-d6): delta [ppm] = 4.13 (apparent d, IH), 4.47 (m, 3H), 5.14 (dd, 2H), 5.51- 5.63 (m, IH), 5.79-5.90 (m, IH), 7.23 (d, 2H), 7.30 (t, IH), 7.45 (t, 2H), 7.79 (br m, 2H), 7.97 (br s, IH), 8.19 (d, IH). LCMS (method 3): Rt 1.75 min MS (ESI): [M + H]+ = 458.0

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 79463-77-7.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; MOWAT, Jeffrey Stuart; STELLFELD, Timo; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; BRUMBY, Thomas; BARACK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (186 pag.)WO2016/91845; (2016); A1;,
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